Watching with Wendy

I’d let my assistant Diane have the day off. Fridays were slow and we had college, summer help available should I need anything. After lunch, I finished all my work, but stayed because I wanted to reward myself with a few private hours on my computer. I put my phone on do-not-disturb.

I logged onto the site that I’d subscribed to after getting my new system. The fee was high, but worth the quality movies provided. I opened a new movie under my favorite category, “Secretary and Boss”, and was soon enjoying my private discretion.

Totally absorbed, I didn’t notice Wendy, one of our summer students; enter until she’d come beside side my desk to ask, “Mr. Barnes, can I do anything for you.”

Caught in the act, I was slow to react in moving my pointer and clicking off the screen. I could tell from the look on Wendy’s face that she’d seen enough. Switching to damage control, I said, “Sorry, Wendy. I didn’t hear you come in and hope you don’t..”

Interrupting, she spoke in awkward rapid sentences, “Mr. Barnes, it’s my fault. I should’ve knocked before I came in looking for something to do. Besides, you weren’t doing anything wrong. Lots of people like watching porn movies. I like them too. Sometimes, when everyone leaves for lunch, I stay in and watch some free clips. I think I’ve even seen some like the one you were watching. I won’t tell anyone. I need the money from this job for school too much.”

She stopped, looking nearly as guilty as I felt. I felt she was sincere and it gave me an idea. I carefully chose my words to say, “Don’t worry, Wendy. The fault is mine, not yours. I’ve been careless. I’m certainly not going to say anything. From what you say, there is something you could do to make us both feel better.”

Unease faded from her face replaced by a puzzled look as she asked, “What’s that?”

“You could lock the door and watch the movie with me”

She gave a broad smile, darted to my office door and dragged one of my visitor’s chairs around my desk. It was the first time that I noticed her pert, little figure. It fit her age, no longer a child and a few years shy of the full blossom of womanhood.

I restarted movie after explaining that we’d see a whole movie, not just a clip. We watched silently through the business-like opening and remained silent as the couple engaged in foreplay. When the secretary’s blouse and bra came off, Wendy asked, “Is it OK if we talk while we watch?”

“That’d be fine, even make it more fun. Just as long as we keep our voices down, we’ll be fine.”

“Oh, good. I was thinking how they use busty women in these films, probably because most men like big breasts. I’m only a size 32B and don’t think I’ll get much bigger without surgery. But, I’m afraid to do it. Would you, Mr. Barnes?”

I glanced sideways at Wendy’s chest and said, “I really never thought about before. If I were a woman, I wouldn’t. You’re young and I’m sure you’ll have plenty of lovers who’ll like you as you are.”

“You really think so, Mr. Barnes?”

“I’m sure of it, Wendy.” I turned my eyes back to the screen not wanting her to get uncomfortable with my eyes on her blouse.

A few silent minutes passed as the boss licked and sucked the secretary’s breasts. Hiking her skirt, the secretary lifted a leg onto a chair to reveal she wore only a garter belt and stockings. The camera zoomed in to her perfectly shaved crotch. The boss’ hand came in to fondle her to moaning. Wendy commented, “Most of the gals are shaved. I did it once. But, it itched so I let it grow back and now I just trim it nice. Mr. Barnes, which do you like – shaved or unshaved?”

“I think it’s more sensual when the woman isn’t shaved, but not real hairy. I enjoy feeling soft pubic hair on my fingers and hand. For me, it adds something to my enjoying my partner. Even giving oral pleasure, it’s kind of stimulating.”

A wider shot followed with the secretary, discarding her skirt, kneeling and undoing the boss’ pants. The camera zoomed in to capture the secretary using her hands and mouth to stimulate the boss to full erection. A quick dip of the lens showed the secretary rubbing herself.

The lengthy scene, with Wendy near, brought on my own arousal. I shifted several times attempting to allow more room for my erection, uncomfortably confined by my clothing.

Though my eyes stayed on the screen, I heard the creaking of Wendy’s chair and motion at the corner of my eye. Wendy was fidgeting too. Turning slightly, I saw she couldn’t keep her arms and hands still. She’d rest her elbows on her chair’s arms only to lift them a few seconds later and run her hands down her skirt over the tops of her thighs. When she reached her knees, she’d reverse to draw her hands back up, all the way up to the skirt’s waist. After repeating the cycle about five times, she sighed and said, “Mr. Barnes, could you stop the movie a minute. I want to ask you something.”

I paused it, swerved my chair to her and asked, “There, what is it?”

“Mr. Barnes, the movie is so good. Maybe, a little too good because I’m really getting turned on. I was thinking how we could enjoy it even more if we were able to touch ourselves while we watched.” Hesitating and dropping her eyes, she noticed the obvious bulge in my pants. She smiled and continued, “Even better.. Since the door is locked.. we could take some of our clothes off.”

Her provocative suggestion presented another quandary. I’d found a solution to dispel my fears, and possible personal damage, only to be confronted with more. Yet, I couldn’t resist the temptation of her idea. My first thought was to make a firm refusal. But, the temptation was irresistible and I replied, “I like your idea. Wendy. But promise me, because I’m not as big as the men in these movies, that you won’t do anything to embarrass me.”

Unable to hide her excitement, she said, “Why would I? You made me feel good about not being big breasted as the gals in these movies. I’m sure they choose the guys the same way.”

Not waiting for me to respond, she sprang up and began removing her skirt. My only choice was to follow. I was slower and, by the time I dropped my pants, she was pulling off her pantyhose and panties. She giggled as she sat back down to completely shed and kick away her discarded clothing. Grinning with glee, she rested her elbow on the chair arms and looked up as if delighted to have exposed herself to me.

Despite her glaring enthusiasm and assuring comment, I was still feeling some embarrassment. She watched as I took a deep breath and pushed off my underpants. My limp cock hung in full view. Her grin didn’t waver as she said, “Mr. Barnes, you’re not SMALL! Even soft, you look great to me. How do I look to you?”

She scooted to the edge of her seat and spread her legs to offer me a full view of her exposed lower half. Her pale skin looked soft and creamy smooth. Her pubic hair, as she’d mentioned earlier, was carefully trimmed above and around the cleft of her womanhood. I couldn’t stay my arousal and knew it showed as I complimented her, “Wendy, you’re lovely.”

“Thanks, Mr. Barnes. This is going to make everything so much more exciting.” I felt myself reacting, as any man would in being alone and nearly naked with an adult woman thirty years younger. Wendy’s bubbly reaction to my bare, my most private body parts overwhelmed all my fears. My shaft jerked and started to swell.

My reaction wasn’t unnoticed by Wendy. Her eyes stayed on my growing hardness as I kicked away my pants and underpants before sitting down. As I reached for the mouse, she topped me, “Wait. Before we restart the movie.. would it be OK.. if I touched you just a little? You can touch me too, if you’d like.”

Teetering between lust and caution, I agreed, “I’d like that, but just a little. I don’t think either of us want to start something that’d ruin our fun.”

“It won’t, Mr. Barnes. It’ll be fine.”

We both reached out to gently touch. Her fingertips swept down my full length as mine furrowed through her soft pubic hair, barely skimming her skin at their base. I moved on to run my fingertips down, over her warm puffy outer lips. She grazed my domed head, circled around and across it and traced its smooth ridge. I grew larger with a surge of desire that threatened my resolve.

I nearly lost control when my fingertips found her even warmer entryway. I yanked my hand back. “Let’s get back to the movie.”

Wendy was slower to remove hers. She didn’t withdraw until mine grasped the mouse, moved the pointer to the start button and clicked.

The secretary licked her boss until he was fully engorged. She took half his length into her mouth. Her checks hollowed as she sucked hard and bobbed her head on his glistening saliva-covered cock. The camera drifted down to show she was rubbing a hand over her slit. Moving back up, the secretary throated his full length.

Just having Wendy at my side, without touching her, was incredibly erotic. I swathed my hardened shaft and scrotum and, without checking, was certain she was doing the same. The early danger in our touching averted, I was now glad I’d agreed with her suggestion.

Speaking over the boss’ groans, Wendy said, “I’ve tried to deep-throat a couple of times but I always gag.”

“Lots of women don’t like oral sex, either giving or receiving. I’m sure not all the ones that enjoy giving it can deep-throat. Personally, I enjoy both giving and receiving. It’s just an individual’s preference.” Wendy didn’t see me turn to reply, her eyes were glued to the screen. She hadn’t settled back in her seat and was stretched out with her legs spread wide open. Both hands roved over her bare thighs, dipped into her crotch and swept across her patch of hair on her mound. I looked back without her noticing that I’d looked.

The secretary rose and planted one leg on a chair. The boss groped her two smooth rear cheeks before the camera zoomed in. His cock head rubbed up and down her puffy wet pussy lips before he slipped it into her. Wendy said, “I love the close shots of the guy’s cock going in for the first time.”

She let out a short, nervous laugh before continuing, “Unless they only have time for a fun ‘quicky’, I can’t see how anyone would want sex standing up. I never tried, I’m afraid I’d lose my balance. You ever do it standing up, Mr. Barnes?”

“No I haven’t, even when I was young and single. Mrs. Barnes and I really enjoyed sex the first ten years after we married. We enjoyed each other often, trying lots of different ways but not standing up. Over the years, her interest in sex has diminished. We still have it once in a while. I think she does it only because it’s her duty. I miss the intimacy but never had an affair. It’s safe watching movies like this one. They don’t even compare to real sex but I enjoy them. Of course, watching with you and both of us half naked, is thrilling new experience for me. I can’t thank you enough.”

Wendy’s hand came to rest on my bare thigh as she said; “This is great for me too. It’s so wickedly exciting.”

I looked down when her hand found my inflated staff and faced her when she gave it a few light swipes. She took my wrist and guided my hand over her warm center. We both smiled. She winked and the two of us returned our attention to the screen.

Both of us quietly played with each other as the movie couple repositioned. The secretary sat on the desk’s edge with her legs spread and laid back. The boss hoisted one leg to his shoulder as he inserted his cock and resumed their encounter. The camera jumped between the two faces and close-ups of his assault on her pussy.

I let Wendy’s hand replace mine around my shaft. She gently stroked it using only her fingers. I ran casually brushed her soft pubic hair and ran my fingertips up and down her groove. Her other hand crept under the base of my palm and began to circle and press where I guessed her clit to be. I set my top knuckles on her seat with my fingers curled inward. I easily found and plied the damp, spongy softness of her opening’s flaps.

The secretary lowered her leg then pulled both legs back and out. Her hands gripped the desk’s edge as he leaned forward, slipped his arms under her knees and continued until he’d reached around to grasp her breasts. Tweaking her nipples, he kissed her hard on the lips.

Wendy commented, “I just love that position. The kissing, those wonderful pleasure sensations shooting from my nipples to my center as I feel his hard rod trusting in and out of me.”

From the vibrations caused by her shortened breath, I knew Wendy was getting more excited. At the same time, her touching, feathery stroke strengthened and became uneven. occasional squeeze of my now full-hardened shaft. I couldn’t help pressing my fingers harder into her wet, velvety pleasure cleft. She gave me one hard pump before releasing hold and nearly moaned, “Slip your fingers inside me.”

I swirled my chair around to see Wendy using the hand she’d reclaimed to push up her top and bra. Her eyes closed when I slid two fingers easily in and swirled them around against her slippery, spongy inner walls.

She plied, tweaked and pulled at the nipples of her perky little breasts. She whispered pleadingly, “I’m so close. Bring me there. Pump me with your fingers.”

I made a one deep plunge, measuring her depth and then snapped my wrist in rapid strokes. Using my other hand to stroke my hardness, I watched her whole body writhe and strain. She sucked her lower lip in as far as she could and clenched her teeth to muffle her moans. Her legs flapped, clamping and unclamping my hand. Her nostrils flared in breathing.

Wendy’s hips bolted up against my pumping hand. I held firm through several strong jolts lifting her off her seat and warm liquid flowed onto my buried fingers. She settled down and stilled as a series of slowly diminishing shudders followed. Her eyes opened and she said, “That was a wonderful orgasm. Thank you, Mr. Barnes.”

Wendy righted herself, pushing back into her chair. She saw I was still hard and blurted, “Mr. Barnes, you’re still hard. It’s only fair that, since you’ve gotten me off, I can do the same for you.”

She fell out her chair to her knees before me as I said, “But, Wendy, that could be messy.”

Her one hand cupped my balls while her thumb and forefinger surrounded the base of my shaft. She smiled in looking up to say, “No it won’t. You can cum in my mouth and I’ll swallow all of it.”

She hungrily licked my entire shaft then swirled her tongue over my dome and around the bottom mushroom-like ridge. Rolling my balls in her hand, she took me into her mouth. Vigorously sucking and pumping, Wendy brought me to an intense release quickly. Ironically, as I emptied into her mouth, the boss gave the secretary a drenching facial.

Wendy and I watched three more movies together. We pleasured each other every time without ever going beyond oral stimulation. The time came for her to leave, returning to college for her senior year. We were both a little saddened. Luckily, I found an appropriate card to give her. It bore a picture of a couple in the midst of steamy sex. I slipped $500 into the card – a small token of my appreciation for what she’d given me.

For a few months, we exchanged emails. They stopped, as I knew they would. I still had the memories and they came back each time I watched a movie.